126683-99-6

Basic information

• Product Name: DI-1-ADAMANTYLPHOSPHINIC CHLORIDE
• Synonyms: DI-1-ADAMANTYLPHOSPHINIC CHLORIDE;Di-1-adamantylphosphinicchloride,98%;Bis(1-adamantyl)phosphinic chloride;Di-1-adamantylphosphinyl chloride;P,P-Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphinic chloride;1-[1-adamantyl(chloro)phosphoryl]adamantane;Di(adamantan-1-yl)phosphinic chloride;phosphinic chloride
• CAS NO: 126683-99-6
• Molecular Formula: C₂₀H₃₀ClOP
• Molecular Weight: 352.88
• Product Categories: organophosphine ligand;Achiral Phosphine;Alkyl Phosphine;P-Cl
• Mol File: 126683-99-6.mol

Chemical Properties

• Melting Point: 214°C
• Boiling Point: 498.0±12.0 °C(Predicted)
• Appearance: white/crystal
• Density: 1.23
• Sensitive: moisture sensitive
• CAS DataBase Reference: DI-1-ADAMANTYLPHOSPHINIC CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DI-1-ADAMANTYLPHOSPHINIC CHLORIDE(126683-99-6)
• EPA Substance Registry System: DI-1-ADAMANTYLPHOSPHINIC CHLORIDE(126683-99-6)

Safety Data

• Hazardous Substances Data: 126683-99-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Di-1-adamantylphosphinic chloride serves as a reagent for the preparation of a variety of phosphine oxides and phosphine sulfides. Its steric properties make it particularly useful in the synthesis of these compounds, facilitating specific reaction pathways and outcomes.
Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, Di-1-adamantylphosphinic chloride is utilized for the preparation of chiral phosphine ligands. These ligands are essential for enantioselective reactions, where the compound contributes to the selective formation of one enantiomer over another, a critical aspect in the production of pharmaceuticals and agrochemicals.
Used in Pharmaceutical and Agrochemical Industries:
Di-1-adamantylphosphinic chloride acts as a precursor in the synthesis of phosphinic acid derivatives. These derivatives hold potential applications within the pharmaceutical and agrochemical sectors, where they may contribute to the development of new drugs and pesticides.
Used in Flame Retardants and Polymer Additives:
Furthermore, Di-1-adamantylphosphinic chloride has been investigated for its potential use in the development of flame retardants and as additives in polymers. Its incorporation could enhance the performance and safety characteristics of these materials, particularly in industries where flame resistance and material durability are paramount.

Upstream product

• 768-95-6 1-adamanthanol 
• 23906-91-4 (1-adamantyl)dichlorophosphine 
• 7446-70-0 aluminum (III) chloride 
• 281-23-2 adamantane 
• 7719-12-2 phosphorus trichloride 
• 131211-27-3 di-1-adamantylphosphine 
• 768-90-1 1-Adamantyl bromide 
• 57680-77-0 adamantylmagnesium bromide 

Downstream Products

• 157282-19-4 di-1-adamantylchlorophosphane 
• 131266-79-0 bis(1-adamantyl)phosphine oxide 
• 131211-27-3 di-1-adamantylphosphine 

Relevant articles and documents

CYCLOPENTADIENYL/ADAMANTYL PHOSPHINIMINE TITANIUM COMPLEXES

Provided in this disclosure are titanium complexes that contain 1) a cyclopentadienyl ligand; 2) an adamantyl-phosphinimine ligand; and 3) at least one activatable ligand. The use of such a complex, in combination with an activator, as an olefin polymerization catalyst is demonstrated. The catalysts are effective for the copolymerization of ethylene with an alpha olefin (such as 1-butene, 1-hexene or 1-octene) and enable the production of high molecular weight copolymers (Mw greater than 25,000) at high productivity under solution polymerization conditions.

CYCLOPENTADIENYL/ADAMANTYL PHOSPHINIMINE ZIRCONIUM AND HAFNIUM COMPLEXES

Provided in this disclosure are zirconium and hafnium complexes that contain 1) a cyclopentadienyl ligand; 2) an adamantyl-phosphinimine ligand; and 3) at least one other ligand. The use of such a complex, in combination with an activator, as an olefin polymerization catalyst is demonstrated. The catalysts are effective for the copolymerization of ethylene with an alpha olefin (such as 1-butene, 1-hexene, or 1-octene).

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

Catalyst system

The present invention provides a catalyst system capable of catalyzing the carbonylation of an ethylenically unsaturated compound, which system is obtainable by combining: a) a metal of Group VIB or Group VIIIB or a compound thereof,b) a bidentate phosphine, arsine or stibine ligand, andc) an acid, wherein the ligand is present in at least a 2:1 molar excess compared to the metal or the metal in the metal compound, and that the acid is present in at least a 2:1 molar excess compared to the ligand, a process for the carbonylation of an ethylenically unsaturated compound, a reaction medium, and use of the system.

Crystal and molecular structures of di-1-adamantylthiophosphinic chloride, p,p-diphenyl-n-benzyl phosphinothioic- and selenoic- amides

Synthesis and X-ray structural determination of three phosphorus compounds are reported. (3b) is monoclinic P2(1)/c with a = 11.852(1), b = 12.825(1), c = 12.445(1) A, β = 103.693(1)°; (4a) and (4b) are monoclinic P2(1)/n with a = 12.1422(16), b = 9.0860(

Production of novel phosphane ligands and use in catalytical reactions

The invention relates to novel phosphane ligands of formula (Ia) and (Ib): (adamantyl)nP(alkyl)m(1a); (adamantyl)o(Alkyl)qP (alkylen′)P(adamantyl)r(alkyl)s (1b), wherein adamantyl represents an adamantyl radical (IIa, IIb) bonded to the phosphorous atom in position 1 or 2. The invention also relates to the production and use of the above-mentioned ligands in the presence of transitional metal compounds of the 8th. Subgroup of PSE for catalytic reactions, particularly for the refining of halogen aromatics for producing aryl olefins, dienes, diarylene, benzoic acid and acrylic acid derivatives, aryl alkanes and also amines.

ORGANOPHOSPHORUS COMPOUNDS WITH TERTIARY ALKYL SUBSTITUENTS. VI: A CONVENIENT METHOD FOR THE PREPARATION OF DI-1-ADAMANTYLPHOSPHINE AND DI-1-ADAMANTYLCHLOROPHOSPHINE

Di-1-adamantylchlorophosphine 3 is obtained by a three step sequence from commercially available adamantane.Despite the bulky 1-adamantyl groups at the phosphorus atom, it reacts readily with water to give di-1-adamantylphosphine oxide 4.Key words: 1-Adamantyl phosphorus compounds, Friedel-Crafts reaction, H/D-exchange, NMR.

Organophosphorus Compounds with Tertiary Alkyl Substituents. III: Synthesis and Reactions of Di-1-adamantyl-Substituted Phosphorus Compounds; Crystal Structure of Di-1-adamantylphosphinic Chloride

The reaction of adamantane with PCl3/AlCl3, followed by hydrolysis, gave (1-Ad)2P(:O)Cl 1, which was converted to (1-Ad)2P(:O)F 2 and (1-Ad)2P(:S)Cl 3 by standard procedures.The structure of 1 was confirmed by a single crystal X-ray structure determinatio

PHOSPHORYLATED ADAMANTANES. XV. PHOSPHORYLATION OF ADAMANTANE WITH P(III) ACID CHLORIDES IN SULFURIC ACID

A new method of introduction of a phosphoryl group into the nodal position of the adamantane nucleus was developed, in which sulfuric acid was used instead of aluminum halides to generate the adamantyl cation in reactions of Br-, OH-, and ONO2-substituted adamantanes and phosphonous and phosphorous chlorides. Relative rates of the hydride shift and skeletal isomerization were qualitatively estimated. Under comparable conditions the rate of the hydride shift in 2-adamantyl carbocation -> 1-adamantyl carbocation is substantially higher than that in the isomerization 1-ethyl-3-adamantyl carbocation -> 1,3-dimethyl-5-adamantyl carbocation.